Organosilicon compounds having aminoaryl groups are know per se, and examples of several methods suitable for synthesis of these compounds have been published. For example, Journal of Organic Chemistry, No. 51, page 2434 (1986) discloses a method of synthesis of a p-dimethylmethoxysilylaniline or p-methylmethoxyphenylsilylaniline by preparing a Grignard reagent from an N,N-bis(trimethylsilyl)-p-bromoaniline and deprotecting [the obtained product] with methanol after reaction with a dimethyldichlorosilane or diphenyldichlorosilane. In this example, however, a Grignard reagent is used also for synthesis of the N,N-bis(trimethylsilyl)-p-bromoaniline, and since the low-efficient Grignard reaction has to be repeated twice, the aforementioned method is not suitable for commercial use.
On the other hand, practical examples of Japanese Patent Application Publication (hereinafter Kokai) H8-99979 disclose a specific method of synthesis of N,N-bis(trimethylsilyl) bromoaniline for use as a starting material. However, this method is based on the use of N-trimethylsilyldiethylamine which is a readily available material. Alternatively, the method requires specific synthesis of N-trimethylsilyl-p-bromoaniline which is not easy to perform.
Furthermore, Synthetic Communication, No. 16, p. 809 (1986) discloses a method of synthesis of 4-dimethylmethoxysilyl-2,6-diethylaniline. This method, however, cannot be implemented on an industrial scale since it utilizes an organic lithium agent that is even less efficient than the Grignard reagent and therefore requires that the synthesis reaction be conducted in two stages.
Journal of Organic Chemistry, No. 66, p. 7449 (2001) discloses a coupling reaction that is conducted between a p-iodoaniline and a trimethoxysilane in the presence of a catalyst. This method is rather impractical for industrial application since it requires the use of a large mount of an expensive palladium catalyst.